ISSN:
0947-3440
Keywords:
C-Glycosides
;
Henry condensation
;
α-Aminoalkyl C-glycosides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The condensation of 4,6-O-benzylidene-D-glucopyranose (1) with nitroethane gave the diastereomeric α-nitroethyl„α“ refers to C-1 of the alkyl substituent; see 2 in Scheme 1. β-C-glucosides 2 (minor), and 6. The latter was only obtained pure by an acetylation-deacetylation procedure and was reduced by a mixture of elemental Fe0/Ni0 in aqueous THF under CO2 to α-aminoethyl β-C-glucoside 7, with retention of the 4,6-O-benzylidene blocking group. Acetylation of 2 produced an open-chain compound 3. An oxime derivative 5 was separated as a byproduct from the acetylation. The condensation of 1-nitropropane with 1, followed by acetylation, similarly gave diastereomers 8 and 9. Deacetylation of 8 gave 10.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199507182
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